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The Lighthouse

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Waterfront
Boat Dock
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Nestled in the picturesque Captain's Cove community, this exquisite three-bedroom, two-bathroom waterfront residence represents the pinnacle of sophisticated coastal living. The stunning new construction boasts an airy, well-conceived open floor plan that seamlessly blends indoor refinement with the serene beauty of unobstructed bay views.

The chef's kitchen stands as a culinary sanctuary, where premium finishes and state-of-the-art appliances await the discerning home cook. In the evening hours, the ambient glow of the fireplace creates an atmosphere of unparalleled comfort and tranquility. For entertainment aficionados, each bedroom features a Smart TV—including the primary bedroom suite.

Perhaps most alluring is the property's 4-season room and direct bulkhead access to the bay, with boat dockage available for nautical enthusiasts. One might say this home doesn't just offer a lifestyle—it launches one.

The distinguished community amenities elevate everyday living to resort-quality experiences, featuring both indoor and outdoor swimming pools, a fitness facility, and an on-site restaurant. The adjacent marina and golf course create a playground for those with a passion for waterfront and fairway pursuits.

This exceptional property affords the advantage of being merely 20 minutes from the wild horses and pristine shores of Chincoteague Island, with the Assateague Island National Seashore's and beach just beyond. For those seeking more vibrant diversions, Ocean City's renowned boardwalk and attractions await just 30 minutes away, while Maui Jack's Waterpark offers family entertainment nearby. As one of Coastal Shore's newest offerings, don't sleep on this one. It will book quickly!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Windshadow

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the French doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Hidden Treasure

4 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

"X" marks the spot here at Hidden Treasure. Nestled in a cove along the shoreline of the island's most exclusive neighborhood on the northern end, you'll have everything you need for a perfect family vacation. ENDLESS outdoor space in the form of a long private dock with a large sitting area at the end, huge deck off the living area overlooking the water, a screened in dining area off the deck, and a large shared balcony off of two of the bedrooms on the upper level. The spacious home offers 4 bedrooms and 3 bathrooms. On the ground level you'll find the fully-equipped kitchen with breakfast bar and dining area. The kitchen opens up to the cozy living area, with a fireplace and an unbelievable view of Chincoteague Bay. You'll find plenty of seating for your family, just around the corner is another sitting area for overflow - or if you just want to curl up with a good book alone (no judgement!). Also located on the ground level is a full bath and bedroom with two twins - ideal for putting the little ones to bed but still being able to keep an eye on them. Upstairs you'll find the other 3 bedrooms. The master suite - furnished with a king bed, bath with Jacuzzi soaking tub and shower, flat-screen, and yet another knockout view on the balcony. The balcony runs the length of the house and is shared on the other end with a bedroom with a queen. An additional full bath, and another bedroom with two twins is also found upstairs as well. Crab and fish right off the dock, and enjoy cooking and enjoying your bounty together al-fresco at the screened-in porch on the deck. Or pour yourself a nice chilled beverage and walk down to the end of the dock and wait for the sun to slip under the horizon over Chincoteague Bay - bringing the end to another day of treasured memories made at Hidden Treasure.

- *NEW FOR 2025: Level 2 EV charger!*

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Wildcat Haven

4 Bedrooms
4 Baths & 1 Half
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Only for the discerning traveler, 'Wildcat Haven' is the newest in luxury vacation accommodations on Chincoteague Island. The reverse floor plan is over 2,800 square feet and offers views of the bay and marshlands where wildlife abounds from nearly every room. The first floor features 4 bedrooms, all en-suite with full bathrooms and a large recreational room with second kitchen and waterside deck. The second floor features the main living areas - living room, dining room, kitchen, powder room - as well as another waterside deck and screened porch. If you love to fish and crab, or just sit at the water's edge, you'll LOVE the 500' private pier! Vacationing with a large group? Check out the sister house 'Wildcat Retreat' right next door!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet friendly with fee. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Poole's Cove

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet's heart. The set up of this home offers plenty of room for the whole family, but enough distance for quiet moments to yourself. The Master bedroom suite is located in the main part of the house. Just a few steps through a breezeway brings you to the second part of the home with 2 more bedrooms and bathrooms. The outside stairs will bring you up to a rooftop lounging area to catch some relaxing rays. Also upstairs is an office with the perfect reading nook to curl up and catch up on some reading. This house doesn't just offer you a stay it offers you the full experience. Poole's Cove has undergone a COMPLETE renovation! The entire interior - kitchen, floors, bedrooms, bathrooms, furniture, everything - is all BRAND NEW! The Poole's Cove you've come to know, and love is even better than before. **IMPORTANT NOTE: Because of this home's unique floor plan and railing-less decks, it may not be suitable for younger children.**

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Pocahontas

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Nestled in the vibrant heart of Cape Charles, this exquisite one-bedroom condominium represents bayside town living at its most refined. Recently transformed through meticulous renovation, the home seamlessly blends simplistic sophistication with coastal charm to create an atmosphere of understated luxury.

The thoughtfully designed interior showcases an open living space with a fireplace and large TV, sumptuous primary bedroom featuring a king-size bed that promises restful nights after sun-soaked days. Step through the doors onto your private balcony, where panoramic views of downtown and the marina create an ever-changing tableau of maritime activity and small-town vibrancy.

Culinary enthusiasts will appreciate the full kitchen appointed with premium new appliances, inviting both casual meals and ambitious dinner preparations. The custom-tiled bathroom elevates daily routines to spa-like experiences, reflecting the property's commitment to refined comfort.

Location defines true luxury, and this residence delivers magnificently. Mere blocks from the shimmering shores of the Chesapeake Bay, you'll find yourself effortlessly immersed in the coastal lifestyle. The convenience of having Cape Charles' most coveted attractions just steps from your door cannot be overstated—savor artisanal spirits at the local distillery, browse distinctive boutiques and art galleries, indulge in gourmet ice cream, or select from diverse dining options.

For the discerning individual seeking a harmonious blend of tranquility and accessibility, this sanctuary offers a rare opportunity to embrace the quintessential Cape Charles experience.

PLEASE NOTE: 'Pocahontas' is one of 5 luxury apartments offered within the 'Cape Dunes' complex. This being the case, some amenities and spaces are shared. This includes the washer & dryer, ice maker and roof top terrace. Parking is on-street and not reserved. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

High Tide

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet
Outdoor Shower

We're pleased to be able to offer 'High Tide' as one of our most popular vacation rental selections! The true epitome of a beach house, you'll enjoy the bright, cheery decor and spacious feel of this fabulous home. The downstairs features an open living room (with fireplace and flat-screen TV), dining area and kitchen, as well as over-sized windows and access to the two (yes, TWO!) screened porches. One porch features a wonderful dining set; perfect for dining al fresco. The second spacious porch features a large hammock and nice sectional lounging sofa. As if that's not enough outdoor space, there are also multi-level, open air decks on the front and back of the home! There's also a bedroom (king) and full bathroom downstairs. The upstairs features two additional bedrooms (one with a queen & two twin beds, and the other with a queen & one twin bed), and a full bathroom. Both upstairs bedrooms are enhanced by sliding doors and private balconies. You'll enjoy snippet water views of the Assateague Channel! Don't delay, 'High Tide' books quickly. Please note: As part of the Piney Island Community, this rental includes water access at a shared community location just a short distance from the home.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Virginia Lee

2 Bedrooms
1 Baths & 1 Half
4 Guests
Cape Charles
Internet

Experience vacation living at its finest in this newly renovated two-bedroom, one-and-a-half-bathroom condominium nestled in the heart of Cape Charles. This thoughtfully designed retreat features an open floor plan complemented by a full kitchen with brand-new appliances for the culinary enthusiast.

The inviting living room showcases eye-catching skylights that flood the space with natural light, while a large television and cozy fireplace create the perfect atmosphere for relaxation. The comfortable primary bedroom offers a king bed and connects to a custom-tiled bathroom, while the upstairs bedroom includes an adjoining powder room for added convenience.

What truly distinguishes this property is its spectacular rooftop terrace, complete with a wet bar sheltered by an elegant pergola — ideal for entertaining guests or enjoying breathtaking sunset views over the Chesapeake Bay.

The condo offers unparalleled convenience, situated just blocks from Cape Charles' pristine beachfront and within easy walking distance to the town's vibrant center. Imagine strolling to local restaurants, browsing unique boutique shops and art galleries, or treating yourself at the Cape Charles Distillery — all without needing to use your car.

Whether seeking a peaceful weekend getaway or an extended coastal retreat, this charming condominium offers the perfect blend of modern comfort and small-town bayside living.

PLEASE NOTE: 'Virginia Lee' is one of 5 luxury apartments offered within the 'Cape Dunes' complex. This being the case, some amenities and spaces are shared. This includes the washer & dryer, ice maker and roof top terrace. Parking is on-street and not reserved. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Grandview

4 Bedrooms
4 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to stow away with a book. The dining area is big enough to accommodate large family dinners and the kitchen has been newly remodeled and upgraded! With a breakfast bar and wide open living area, you can be sure to have lasting family moments together. Have your cameras ready to capture the changing tides, wildlife and those crazy family moments that are sure to happen in this lovely home. Grandview offers every amenity from a screened porch, an open deck, long pier with a dock, ceiling fans throughout, wireless internet and much much more! This home also includes the use of 2 kayaks.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Sunkissed Shores

4 Bedrooms
4 Baths
15 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

La Dolce Vita is now SUNKISSED SHORES! Enjoy breathtaking waterfront views and spectacular sunsets from every room in this comfortable luxury waterfront home on Chincoteague Bay! Each of the 4 bedrooms features a private full bath. There are bedrooms on both levels with the master bedroom on the first floor. The MBR suite has a private bath with jacuzzi tub and private waterside balcony. There's also a smaller bedroom with two twins on the first level. The two bedrooms upstairs are private wings off the game room. The game room has two separate gaming tables that young and old alike will enjoy. Checkers with the grandkids! There is bathroom access on this level for guests that use the sleeper sofa in the game room. The kitchen opens to the dining & living room areas which are flanked by floor to ceiling windows & cathedral ceiling. If you're visiting off season, there's a fireplace in the living room for your enjoyment. Off the living room you'll find a large all-weather waterside gazebo that opens out the the decks. It's a perfect spot for your gatherings. Sunkissed Shores is a beautiful home with a well-thought-out floor plan that you'll truly enjoy. And the waterfront area has new bulkheading - you can easily crab, fish and launch kayaks from this area.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Sea La Vie

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Gas Grill
Screened Porch
Pool
Internet

Aptly named, "Sea la Vie" means "Sea Life" or Life at the Beach. This beautifully upgraded three bed, two and a half bath duplex home is nestled in a small, quiet community. Bright, open floor plan allows plenty of sunshine and space to socialize. Relax by the pool after a long day at the beach. Enjoy a bug-free oasis on the screened porch, or grill out on the open deck. First floor bedroom is situated as a private suite with personal full bathroom. Two additional bedrooms upstairs share a second full bathroom. Picnic area out back, community pool just steps out front, you won't run out of things to do! Hosting a group requiring even more space? Rent Sea La Vie's sister, 'Seas The Day', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bed + a Bunk bed with a Twin over Full size bed!**

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Trembling Bay

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

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